I Slept With A Guy On The First Date & Now He’s My Boyfriend

My date showed up on a cold fall night dressed in footy pajamas and thick rimmed glasses. I answered the door in the same exact get up. He’d decided a Halloween party would be a great location for a first date and thought dressing up as “sleepy hipsters” would be totally comfy and conversation-starter worthy. To my surprise, our date didn’t end with an innocent peck on the cheek. In fact, the date didn’t end until the next morning. At least I wore pajamas!

  1. The moment felt right. From the minute we got into his car to head over to the party, he had me laughing. We looked absolutely absurd in our costumes, but we couldn’t resist, considering the slim chances that two people over 21 happened to own adult-sized footy pajamas. The coincidence was just too good and it didn’t stop there. The whole night was a glorious blur of playing goofy drinking games, meeting his friends, and enjoying each other’s company. I felt like we were on our 100th date, not our first. Every moment leading up to us sleeping together on the first date was perfection.
  2. Sex doesn’t define relationships. Here’s the thing — sex can affect relationships in many ways, but I’ve never been in a situation where sex defined my relationships. Sleeping with a guy on the first date isn’t something I’d typically do, but I knew from the beginning this wasn’t a typical date and he wasn’t a typical guy.
  3. There’s nothing wrong with being impulsive. Let me preface this by saying that unsafe sex is not sexy. I always play it safe when it comes to one-night stands or sleeping with a new partner, but I have no shame in doing things at the last moment because I feel like it! Life is too short to be careful and calculated all the time.
  4. I’m a grown up that can make grown up decisions. Despite our childish attire, we were both fully aware of our actions. As fully consenting adults, we decided to sleep with each other on the first date. Simple as that. Doesn’t sound so scandalous when I put it in those terms, does it?
  5. We both made our intentions clear from the beginning. I happened to know this guy for several years before we finally went out. We were more acquaintances than friends, but every time we ran into each other, we had conversations that always left me wanting more. Although I wouldn’t judge someone for sleeping with a total stranger on the first date, he was far from a stranger to me at that point. We both knew we wanted something to come out of this first date before it even began.
  6. He showed me his true colors before it all went down. At one point during our first date, we stumbled across some amateur DJ’ing equipment. We looked at each other and without saying a word, we started a dance party. We were making complete asses of ourselves and I loved every second of it. I couldn’t remember the last time I smiled and laughed so hard. After the party died down and we decided we were in no condition to drive home, we somehow got on the topic of “Lord of the Rings.” It was so dorky and genuine, I couldn’t resist him.
  7. Second date jitters were thrown out the window. After my date dropped me off the next morning, I won’t lie, I was I was feeling a little off. I was hungover as hell, I looked like a hot mess, and I was feeling a little vulnerable. I sat in the back room at work later that day, nursing my hangover, when I got a text from him saying he had just woke up and he had a blast last night. Did I want to grab coffee later? Any doubt that he had just been a one-night stand left my mind and we had a great time rehashing stories from the night before.
  8. I knew we were sexually compatible before we became a couple. Although I don’t believe sex defines a relationship, good sex can certainly improve a relationship! Knowing we were sexually compatible before we made our relationship official is definitely one of the reasons I’ll never feel guilty for sleeping with him on the first date.
  9. We were both waiting for the right person. Before our first date, both of us had been single for quite some time. We’d tried our hand at dating around after college, but neither of us felt any sort of spark until we finally got together. I had just about given up on the dating scene until he came around, and suddenly I was all in and ready to start a new adventure.
  10. We fell in love that night. A little over four years later, that guy who could’ve just been a one-night stand is now my future husband. We still love to sit down and reminisce over how wild we were on our first date, and recently he said something that surprised me a little bit. “You know we fell in love a little bit that night.” I laughed at first — after all, it was only our first date — but I knew he was absolutely right. We did fall in love that night in our own way and looking back now, I don’t regret a thing.
Jessica is a proud Pittsburgher that loves to drink tea and adopt cats in her spare time. She is a self-proclaimed Slytherin and would like to visit Harry Potter World as soon as possible!